TW200848014A - Novel compounds - Google Patents

Novel compounds Download PDF

Info

Publication number: TW200848014A
Authority: TW; Taiwan
Prior art keywords: phenyl; amino; oxy; acetic acid; methyl
Prior art date: 2006-12-15

Application number

TW096147555A

Other languages

English (en)

Chinese (zh)

Inventor

Alessandra Gaiba

Mark Patrick Healy

Christopher Norbert Johnson

Susan Roomans

Steven James Stanway

Martin Edward Swarbrick

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-12-15

Filing date

2007-12-13

Publication date

2008-12-16

2006-12-15 Priority claimed from GB0625098A external-priority patent/GB0625098D0/en

2007-08-03 Priority claimed from GB0715145A external-priority patent/GB0715145D0/en

2007-12-13 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2008-12-16 Publication of TW200848014A publication Critical patent/TW200848014A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 158
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
239000003814 drug Substances 0.000 claims abstract description 11
238000004519 manufacturing process Methods 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 167
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 82
-1 2,3- Difluorophenyl group Chemical group 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
150000001412 amines Chemical class 0.000 claims description 45
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
208000002193 Pain Diseases 0.000 claims description 34
239000000460 chlorine Substances 0.000 claims description 34
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
101150109738 Ptger4 gene Proteins 0.000 claims description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 25
238000011282 treatment Methods 0.000 claims description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
125000001041 indolyl group Chemical group 0.000 claims description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
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YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 12
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
125000000068 chlorophenyl group Chemical group 0.000 claims description 11
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 11
229960002986 dinoprostone Drugs 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
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230000009471 action Effects 0.000 claims description 9
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NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
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125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
208000019695 Migraine disease Diseases 0.000 claims 2
206010027599 migraine Diseases 0.000 claims 2
PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 claims 1
WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
229960001716 benzalkonium Drugs 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
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229910021653 sulphate ion Inorganic materials 0.000 claims 1
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 183
239000000543 intermediate Substances 0.000 description 85
235000019439 ethyl acetate Nutrition 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
239000000203 mixture Substances 0.000 description 57
238000003756 stirring Methods 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
238000000034 method Methods 0.000 description 50
UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 43
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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239000000047 product Substances 0.000 description 23
239000010410 layer Substances 0.000 description 21
239000007787 solid Substances 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
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150000003839 salts Chemical class 0.000 description 20
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 11
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)

TW096147555A 2006-12-15 2007-12-13 Novel compounds TW200848014A (en)

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GB0625098A GB0625098D0 (en)	2006-12-15	2006-12-15	Novel compounds
GB0715145A GB0715145D0 (en)	2007-08-03	2007-08-03	Novel compounds

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US (3)	US8314147B2 (es)
EP (1)	EP2101751A1 (es)
JP (1)	JP5069752B2 (es)
KR (1)	KR20090089868A (es)
AR (1)	AR064361A1 (es)
AU (1)	AU2007331471C1 (es)
BR (1)	BRPI0720254A2 (es)
CA (1)	CA2672631A1 (es)
CL (1)	CL2007003640A1 (es)
CR (1)	CR10849A (es)
DO (1)	DOP2009000124A (es)
EA (1)	EA015931B1 (es)
IL (1)	IL198931A0 (es)
MA (1)	MA30991B1 (es)
MX (1)	MX2009006474A (es)
NO (1)	NO20092314L (es)
NZ (1)	NZ577109A (es)
PE (1)	PE20081579A1 (es)
SG (1)	SG177203A1 (es)
TW (1)	TW200848014A (es)
WO (1)	WO2008071736A1 (es)

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EP2460787A1 (en) *	2007-07-03	2012-06-06	Astellas Pharma Inc.	Amide compounds and their use as PGE2 antagonists.
GB0721611D0 (en)	2007-11-02	2007-12-12	Glaxo Group Ltd	Novel compounds
WO2009085177A1 (en) *	2007-12-19	2009-07-09	Amgen Inc.	Phenyl acetic acid derivatives as inflammation modulators
US8598355B2 (en) *	2008-05-14	2013-12-03	Astellas Pharma Inc.	Amide compound
GB0810313D0 (en) *	2008-06-05	2008-07-09	Glaxo Group Ltd	Novel compounds
GB0810615D0 (en) *	2008-06-10	2008-07-16	Glaxo Group Ltd	Novel pharmaceutical
GB0810617D0 (en) *	2008-06-10	2008-07-16	Glaxo Group Ltd	Novel pharmaceutical
SG179120A1 (en) *	2009-09-29	2012-05-30	Glaxo Group Ltd	Novel compounds
CN104292154A (zh) *	2009-09-29	2015-01-21	葛兰素集团有限公司	新化合物
KR20120093955A (ko)	2009-10-14	2012-08-23	젬머스 파마 인코포레이티드	바이러스 감염에 대한 병용 요법 치료
PH12013500205A1 (en) *	2010-07-30	2017-08-23	Allergan Inc	Compounds and methods for skin repair
US8900571B2 (en)	2010-08-19	2014-12-02	Allergan, Inc.	Compositions and soft tissue replacement methods
US8894992B2 (en)	2010-08-19	2014-11-25	Allergan, Inc.	Compositions and soft tissue replacement methods
US8926963B2 (en)	2010-08-19	2015-01-06	Allergan, Inc.	Compositions and soft tissue replacement methods
EP3061751A1 (en)	2010-09-21	2016-08-31	Eisai R&D Management Co., Ltd.	Pharmaceutical composition
US20120142684A1 (en) *	2010-12-02	2012-06-07	Allergan, Inc.	Compounds and methods for skin repair
EP2814527A1 (en) *	2012-02-16	2014-12-24	Allergan, Inc.	Compositions and improved soft tissue replacement methods
EP2765128A1 (en) *	2013-02-07	2014-08-13	Almirall, S.A.	Substituted benzamides with activity towards EP4 receptors
KR20160042039A (ko)	2013-08-09	2016-04-18	알데릭스, 인코포레이티드	인산염 수송을 억제하기 위한 화합물 및 방법
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- 2007-12-12 JP JP2009540763A patent/JP5069752B2/ja not_active Expired - Fee Related
- 2007-12-12 MX MX2009006474A patent/MX2009006474A/es active IP Right Grant
- 2007-12-12 CA CA002672631A patent/CA2672631A1/en not_active Abandoned
- 2007-12-12 SG SG2011091873A patent/SG177203A1/en unknown
- 2007-12-12 WO PCT/EP2007/063796 patent/WO2008071736A1/en not_active Ceased
- 2007-12-12 US US12/519,219 patent/US8314147B2/en not_active Expired - Fee Related
- 2007-12-12 US US11/954,815 patent/US20080167377A1/en not_active Abandoned
- 2007-12-12 KR KR1020097012174A patent/KR20090089868A/ko not_active Ceased
- 2007-12-12 AU AU2007331471A patent/AU2007331471C1/en not_active Ceased
- 2007-12-12 EP EP07857459A patent/EP2101751A1/en not_active Withdrawn
- 2007-12-12 EA EA200970585A patent/EA015931B1/ru not_active IP Right Cessation
- 2007-12-12 BR BRPI0720254-7A patent/BRPI0720254A2/pt not_active IP Right Cessation
- 2007-12-13 PE PE2007001779A patent/PE20081579A1/es not_active Application Discontinuation
- 2007-12-13 TW TW096147555A patent/TW200848014A/zh unknown
- 2007-12-14 CL CL200703640A patent/CL2007003640A1/es unknown
- 2007-12-14 AR ARP070105631A patent/AR064361A1/es not_active Application Discontinuation
2009
- 2009-05-25 IL IL198931A patent/IL198931A0/en unknown
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- 2009-06-09 CR CR10849A patent/CR10849A/es unknown
- 2009-06-15 MA MA31990A patent/MA30991B1/fr unknown
- 2009-06-16 NO NO20092314A patent/NO20092314L/no not_active Application Discontinuation
2012
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Also Published As

Publication number	Publication date
NO20092314L (no)	2009-08-31
JP2010513242A (ja)	2010-04-30
AR064361A1 (es)	2009-04-01
EP2101751A1 (en)	2009-09-23
CA2672631A1 (en)	2008-06-19
PE20081579A1 (es)	2009-01-01
AU2007331471A1 (en)	2008-06-19
EA200970585A1 (ru)	2009-10-30
DOP2009000124A (es)	2010-03-31
US8314147B2 (en)	2012-11-20
WO2008071736A1 (en)	2008-06-19
US20080167377A1 (en)	2008-07-10
MA30991B1 (fr)	2009-12-01
KR20090089868A (ko)	2009-08-24
MX2009006474A (es)	2009-06-26
BRPI0720254A2 (pt)	2014-01-07
JP5069752B2 (ja)	2012-11-07
EA015931B1 (ru)	2011-12-30
AU2007331471C1 (en)	2013-07-25
SG177203A1 (en)	2012-01-30
CR10849A (es)	2009-08-12
US20100022650A1 (en)	2010-01-28
CL2007003640A1 (es)	2008-07-11
US20130261185A1 (en)	2013-10-03
IL198931A0 (en)	2010-02-17
AU2007331471B2 (en)	2013-01-10
NZ577109A (en)	2011-12-22

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